CA2772790C - Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors - Google Patents
Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors Download PDFInfo
- Publication number
- CA2772790C CA2772790C CA2772790A CA2772790A CA2772790C CA 2772790 C CA2772790 C CA 2772790C CA 2772790 A CA2772790 A CA 2772790A CA 2772790 A CA2772790 A CA 2772790A CA 2772790 C CA2772790 C CA 2772790C
- Authority
- CA
- Canada
- Prior art keywords
- quinoxalin
- alkyl
- phenyl
- piperazin
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 title abstract description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title description 3
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 title description 3
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 title description 3
- 229940043355 kinase inhibitor Drugs 0.000 title description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 212
- 238000000034 method Methods 0.000 claims abstract description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 238000002360 preparation method Methods 0.000 claims abstract description 46
- 238000011282 treatment Methods 0.000 claims abstract description 32
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 238000011321 prophylaxis Methods 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 640
- -1 hydroxyl- Chemical group 0.000 claims description 587
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 147
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 122
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 206010028980 Neoplasm Diseases 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 66
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 24
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 24
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- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
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- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 13
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- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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| EP09075415 | 2009-09-04 | ||
| EP09075415.1 | 2009-09-04 | ||
| PCT/EP2010/005183 WO2011026579A1 (en) | 2009-09-04 | 2010-08-24 | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
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Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| GB201007286D0 (en) | 2010-04-30 | 2010-06-16 | Astex Therapeutics Ltd | New compounds |
| ES2555261T3 (es) | 2010-06-01 | 2015-12-30 | Bayer Intellectual Property Gmbh | Imidazopirazinas sustituidas |
| UY33452A (es) | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| CN103415518A (zh) | 2010-12-17 | 2013-11-27 | 拜耳知识产权有限责任公司 | 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的咪唑并吡嗪 |
| US9284317B2 (en) | 2010-12-17 | 2016-03-15 | Bayer Intellectual Property Gmbh | Substituted imidazo[1,2-a]pyrazines as MPS-1 inhibitors |
| JP2013545779A (ja) | 2010-12-17 | 2013-12-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための６置換イミダゾピラジン |
| JP5822944B2 (ja) | 2010-12-17 | 2015-11-25 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための２置換イミダゾピラジン |
| CA2821834A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| ES2530802T3 (es) | 2010-12-17 | 2015-03-06 | Bayer Ip Gmbh | Imidazopirazinas 6-tiosustituidas para uso como inhibidores de MPS-1 y TKK en el tratamiento de trastornos hiperproliferativos |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| EP2691375B1 (en) | 2011-03-31 | 2016-03-16 | Bayer Intellectual Property GmbH | Substituted benzimidazoles as mps-1 kinase inhibitors |
| ES2545135T3 (es) | 2011-04-06 | 2015-09-08 | Bayer Pharma Aktiengesellschaft | Imidazopiridinas sustituidas y compuestos intermedios de las mismas |
| HRP20150517T1 (hr) | 2011-04-21 | 2015-06-19 | Bayer Intellectual Property Gmbh | Triazolopiridini |
| WO2012160029A1 (en) | 2011-05-23 | 2012-11-29 | Bayer Intellectual Property Gmbh | Substituted triazolopyridines |
| CN102250022B (zh) * | 2011-05-26 | 2013-10-16 | 浙江大学 | 取代喹喔啉胺类化合物及其制备方法和用途 |
| GB201118656D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118654D0 (en) * | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
| GB201118675D0 (en) | 2011-10-28 | 2011-12-14 | Astex Therapeutics Ltd | New compounds |
| UA112096C2 (uk) | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
| CN104284896B (zh) | 2012-03-14 | 2016-06-01 | 拜耳知识产权有限责任公司 | 取代的咪唑并哒嗪 |
| GB201209609D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
| ES2704744T3 (es) | 2012-06-13 | 2019-03-19 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| CA2878481A1 (en) | 2012-07-10 | 2014-01-16 | Bayer Pharma Aktiengesellschaft | Method for preparing substituted triazolopyridines |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
| GB201307577D0 (en) | 2013-04-26 | 2013-06-12 | Astex Therapeutics Ltd | New compounds |
| CN104140395B (zh) * | 2013-05-08 | 2018-07-24 | 中国医学科学院药物研究所 | 丁炔酰胺衍生物及其制法和药物组合物与用途 |
| WO2014195274A1 (en) * | 2013-06-07 | 2014-12-11 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines |
| RS56034B1 (sr) | 2013-06-11 | 2017-09-29 | Bayer Pharma AG | Derivati prolekova supstituisanih triazolopiridina |
| MX373150B (es) | 2014-03-26 | 2020-04-21 | Astex Therapeutics Ltd | Combinaciones de un inhibidor del factor de crecimiento de fibroblasto (fgfr) y un inhibidor del receptor del factor de crecimiento 1 similar a insulina (igf1r). |
| JP6752715B2 (ja) | 2014-03-26 | 2020-09-09 | アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | 組合せ |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| TWI719960B (zh) | 2015-02-10 | 2021-03-01 | 英商阿斯迪克治療公司 | 新穎組成物 |
| MX373169B (es) | 2015-02-20 | 2020-04-24 | Incyte Holdings Corp | Heterociclos bicíclicos como inhibidores de receptores del factor de crecimiento fibroblástico (fgfr). |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| US10478494B2 (en) | 2015-04-03 | 2019-11-19 | Astex Therapeutics Ltd | FGFR/PD-1 combination therapy for the treatment of cancer |
| FI3283642T3 (fi) | 2015-04-17 | 2024-01-11 | Crossfire Oncology Holding B V | Prognostisia biomarkkereita ttk-inhibiittorikemoterapiaan |
| JP2018525371A (ja) * | 2015-07-30 | 2018-09-06 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アリール置換された二環式ヘテロアリール化合物 |
| AU2016328693B2 (en) | 2015-09-23 | 2021-03-11 | Janssen Pharmaceutica Nv | Bi-heteroaryl substituted 1,4-benzodiazepines and uses thereof for the treatment of cancer |
| DK3353177T3 (da) | 2015-09-23 | 2020-08-24 | Janssen Pharmaceutica Nv | Tricykliske heterocykler til behandling af cancer |
| JP6727660B2 (ja) * | 2015-09-30 | 2020-07-22 | 国立大学法人東北大学 | 糖尿病性腎症の判定マーカー |
| TWI691486B (zh) * | 2016-01-29 | 2020-04-21 | 日商東麗股份有限公司 | 環狀胺衍生物及其醫藥用途 |
| AU2017275657B2 (en) | 2016-06-02 | 2021-08-19 | Novartis Ag | Potassium channel modulators |
| US10689362B2 (en) * | 2016-10-10 | 2020-06-23 | Development Center For Biotechnology | Quinoxaline compounds as type III receptor tyrosine kinase inhibitors |
| JP7106572B2 (ja) * | 2016-12-20 | 2022-07-26 | ブリストル－マイヤーズ スクイブ カンパニー | 免疫調節剤として有用な化合物 |
| PL3571193T3 (pl) | 2017-01-23 | 2022-04-25 | Cadent Therapeutics, Inc. | Modulatory kanału potasowego |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| CN107935944B (zh) * | 2017-10-31 | 2021-12-21 | 广西师范大学 | 具有抗肿瘤活性双芳基脲喹喔啉衍生物及其合成方法 |
| MA52493A (fr) | 2018-05-04 | 2021-03-10 | Incyte Corp | Sels d'un inhibiteur de fgfr |
| CR20200590A (es) | 2018-05-04 | 2021-04-26 | Incyte Corp | Formas sólidas de un inhibidor de fgfr y procesos para prepararlas |
| JP7542538B2 (ja) | 2018-09-18 | 2024-08-30 | ニカング セラピューティクス， インコーポレイテッド | Ｓｒｃホモロジー－２ホスファターゼ阻害剤としての縮合三環式環誘導体 |
| EP3870291A1 (en) | 2018-10-22 | 2021-09-01 | Cadent Therapeutics, Inc. | Crystalline forms of potassium channel modulators |
| TW202043205A (zh) | 2018-12-31 | 2020-12-01 | 美商拜歐米富士恩有限公司 | Menin-mll相互作用之抑制劑 |
| EP3906026A4 (en) | 2018-12-31 | 2022-10-19 | Biomea Fusion, LLC | IRREVERSIBLE INHIBITORS OF MENIN-MLL INTERACTION |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TWI891666B (zh) | 2019-10-14 | 2025-08-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之雙環雜環 |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| BR112022010664A2 (pt) | 2019-12-04 | 2022-08-16 | Incyte Corp | Derivados de um inibidor de fgfr |
| CN110981819B (zh) * | 2019-12-24 | 2022-07-01 | 广西师范大学 | 一种喹喔啉类信号通路抑制剂及其制备方法和应用 |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN111557899B (zh) * | 2020-04-30 | 2023-02-21 | 北华大学 | 一种治疗角膜炎的药物及其制备方法 |
| CN111689951A (zh) * | 2020-06-11 | 2020-09-22 | 西北师范大学 | 一种1-苄基-3-烷基喹喔啉-2(1h)-酮的合成方法 |
| IL305165A (en) | 2021-02-19 | 2023-10-01 | Sudo Biosciences Ltd | Tyk2 inhibitors and uses thereof |
| US12600721B2 (en) | 2021-02-19 | 2026-04-14 | Sudo Biosciences Limited | TYK2 inhibitors and uses thereof |
| CA3207819A1 (en) | 2021-02-19 | 2022-08-25 | Anjali Pandey | Tyk2 inhibitors and uses thereof |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| EP4352059A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2022325861A1 (en) | 2021-08-11 | 2024-02-29 | Biomea Fusion, Inc. | Covalent inhibitors of menin-mll interaction for diabetes mellitus |
| IL310717A (en) | 2021-08-20 | 2024-04-01 | Biomea Fusion Inc | Crystalline form of N-[4-[4-(4-morpholinyl)-7H-PYRROLO[2,3-D]PYRIMIDIN-6-YL]PHENYL]-4-[[3(R)-[(1-OXO ] -2-PROPEN-1-YL)AMINO]-1-PIPERIDINYL]METHYL]-2-PYRIDINECARBOXAMIDE, IRREVERSIBLE MENIN-MLL INHIBITOR FOR CANCER TREATMENT |
| WO2024155710A1 (en) | 2023-01-18 | 2024-07-25 | Biomea Fusion, Inc. | Crystalline forms of n-[4-[4-(4-morpholinyl)-7h-pyrrolo[2,3-d]pyrimidin-6- yl]phenyl]-4-[[3(r)-[(l-oxo-2-propen-l-yl)amino]-l-piperidinyl]methyl]-2-pyridinecarboxamide as a covalent inhibitor of menin-mll interaction |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| AUPN842196A0 (en) * | 1996-03-05 | 1996-03-28 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| DE69828607T2 (de) | 1997-05-28 | 2006-01-05 | Aventis Pharmaceuticals Inc. | CHINOLIN- UND CHINOXALIN-VERBINDUNGEN DIE DEN VON BLUTPLÄTTCHEN ABSTAMMMENDEN WACHSTUMSFAKTOR UND/ODER PDGF- UND P56lck-TYROSIN-KINASE HEMMEN |
| AU2003290734A1 (en) | 2002-11-27 | 2004-06-23 | Eli Lilly And Company | Novel compounds as pharmaceutical agents |
| JP2004346016A (ja) | 2003-05-22 | 2004-12-09 | Otsuka Chemical Co Ltd | トリフルオロメチルキノキサリン化合物、その製造方法、及び有害生物防除剤 |
| CN101528231A (zh) | 2006-08-16 | 2009-09-09 | 埃克塞利希斯股份有限公司 | 在癌症的治疗中使用pi3k和mek调控剂 |
| PE20090288A1 (es) * | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| WO2009021083A1 (en) * | 2007-08-09 | 2009-02-12 | Smithkline Beecham Corporation | Quinoxaline derivatives as pi3 kinase inhibitors |
| US20100305133A1 (en) * | 2007-11-30 | 2010-12-02 | Smithkline Beecham Corporation | Prolyl Hydroxylase Inhibitors |
| JP5599783B2 (ja) * | 2008-05-30 | 2014-10-01 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| PE20121148A1 (es) * | 2009-08-17 | 2012-09-07 | Intellikine Llc | Compuestos heterociclicos y usos de los mismos |
-
2010
- 2010-08-24 CA CA2772790A patent/CA2772790C/en not_active Expired - Fee Related
- 2010-08-24 JP JP2012527219A patent/JP5728683B2/ja not_active Expired - Fee Related
- 2010-08-24 CN CN2010800490392A patent/CN102596932A/zh active Pending
- 2010-08-24 WO PCT/EP2010/005183 patent/WO2011026579A1/en not_active Ceased
- 2010-08-24 EP EP10747595A patent/EP2473498A1/en not_active Withdrawn
- 2010-08-24 US US13/393,583 patent/US9340528B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP5728683B2 (ja) | 2015-06-03 |
| JP2013503824A (ja) | 2013-02-04 |
| CA2772790A1 (en) | 2011-03-10 |
| EP2473498A1 (en) | 2012-07-11 |
| US9340528B2 (en) | 2016-05-17 |
| CN102596932A (zh) | 2012-07-18 |
| WO2011026579A1 (en) | 2011-03-10 |
| US20120263708A1 (en) | 2012-10-18 |
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